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Search results; Over 1,000 homes in Middleburg

Home in Middleburg
Home away from home
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
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Farm stay in Middleburg
A Private Loft at Grand Landings Equestrian Center
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 276 reviews
Guest favourite
Flat in Middleburg
Florida Postcard Getaway
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Middleburg
Sunset Pond Views| Perfect For Families
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Orange Park
Game Room + Fenced Backyard | Rococo Retreat | 3BR
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Farm stay in Middleburg
Haystays Farm-Cozy, Charming, Country, Modern Home
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 240 reviews
Superhost
Home in Orange Park
Modern Open Concept 3/2 Retreat
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
New place to stay
Top guest favourite
Home in Middleburg
Charming Southern Country Retreat
6 bedrooms, 8 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Orange Park
Dogwood Stay: Near the Lake
3 bedrooms, 3 king beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 71 reviews
Top guest favourite
Yurt in Middleburg
Pasture Bedtime Yurt
1 bedroom, 5 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Middleburg
NEW Spacious 5/2 Huge Yard Fence 6 TVs Beach45min
5 bedrooms, 10 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Place to stay in Orange Park
Beautiful 3 bedroom 2 bathroom waterfront home
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 137 reviews
Top guest favourite
Home in Jacksonville
4bd 2 bth Home in Oakleaf area! W/Tesla Charger
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Orange Park
Luxury Home w/ Glass Room & Patios
4 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
4.9 out of 5 average rating, 263 reviews
Guest favourite
Home in Orange Park
Spacious family hangout spot
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Townhouse in Orange Park
New 3BR Townhome, King Suite + Small Dogs
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Fleming Island
Rustic Owl in Fleming Island with 2 Kings
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Place to stay in Green Cove Springs
Waterfront Sanctuary
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 64 reviews
Guest favourite
Home in Middleburg
Creek House hideaway NEW HOT TUB !
3 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
4.9 out of 5 average rating, 59 reviews